Ring opening with kinetic resolution of azlactones by Ti-TADDOLates

Tetrahedron

Volumn 55, Issue 3, 1999, Pages 723-738

  Gottwald, Konstanze ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Azlactones; Kinetic resolution; Oxazol 5 (4H) ones; Ti TADDOLates

Indexed keywords

AZLACTONE; ESTER; LACTONE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; KINETICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033556055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01064-3     Document Type: Article

References (74)

1. Plöchl J. Ber. Dtsch. Chem. Ges. 1883;16:2815.
2. Erlenmeyer E. Justus Liebigs Ann. Chem. 1893;275:1.
3. Rao YS, Filler R. In: Turchi IJ, editor. Oxazoles. New York: Wiley, 1986:361.
4. Maryanoff BE. In: Turchi IJ, editor. Oxazoles. New York: Wiley, 1986:988.
5. Noyori R, Tokunaga M, Kitamura M. Bull. Chem. Soc. Jpn. 1995;68:36.
6. Ward RS. Tetrahedron: Asymmetry 1995;6:1475.
7. Caddick S, Jenkins K. Chem. Soc. Rev. 1996;25:447.
8. Stecher H, Faber K. Synthesis 1997:1.
9. Eliel E. Stereochemistry of Carbon Compounds. New York: McGraw-Hill, 1962.
10. Kemp DS. In: Gross E, Meienhofer J, editors. The Peptides. New York: Academic Press, 1979:315.
11. Benoiton NL. In: Gross E, Meienhofer J, editors. The Peptides. New York: Academic Press, 1983:218.
12. De Jersey J, Runnegar MTC, Zerner B. Biochem. Biophys. Res. Commun. 1966;25:383.
13. De Jersey J, Zerner B. Biochemistry 1969;8:1967.
14. De Jersey J. Biochemistry 1970;8:1761.
15. Previero A, Coletti-Previero M-A. C. R. Acad. Sci., Ser. D 1969;268:1798.
16. Coletti-Previero M-A, Kraicsovits F, Previero A. FEBS Lett. 1973;37:93.
17. Daffe V, Fastrez J. J. Am. Chem. Soc. 1980;102:3601.
18. Daffe V, Fastrez J. J. Chem. Soc. Perkin Trans. 2 1983:789.
19. Bevinakatti HS, Newadkar RV, Banerji AA. J. Chem. Soc. Chem. Commun. 1990:1091; Bevinakatti HS,Banerji AA, Newadkar RV, Mokashi AA. Tetrahedron: Asymmetry 1992;3:1505.
20. Bevinakatti HS, Newadkar RV, Banerji AA. J. Chem. Soc. Chem. Commun. 1990:1091; Bevinakatti HS, Banerji AA, Newadkar RV, Mokashi AA. Tetrahedron: Asymmetry 1992;3:1505.
21. Gu R-L, Lee I-S, Sih CJ. Tetrahedron Lett. 1992;33:1953.
22. Crich JZ, Brieva R, Marquart P, Gu R-L, Flemming S, Sih CJ. J. Org. Chem. 1993;58:3252.
23. Turner NJ, Winterman JR, McCague R, Parratt JS, Taylor SJC. Tetrahedron Lett. 1995;36:1113.
24. Steglich W, Weygand F, Barocio de la Lama X. Tetrahedron Suppl. 1966;8:9
25. Steglich W, Frauendorfer E, Weygand F. Chem. Ber. 1971;104:687.
26. Tomida I, Senda S, Kuwabara T, Katayama K. Agr. Biol. Chem. 1976;40:2033.
27. Miyazawa T, Otomatsu T, Higashi K, Yamadat, Kuwata S. Bull. Chem. Soc. Jpn. 1988;61:4161.
28. Obrecht D, Spiegler C, Schönholzer P, Müller K. Helv. Chim. Acta 1992;75:1666.
29. Obrecht D, Bohdal U, Broger C, Bur D, Lehmann C, Ruffieux R, Schönholzer P, Spiegler C, Müller K. Helv. Chim. Acta 1995;78:563.
30. Liang J, Ruble JC, Fu GC. J. Org. Chem. 1998;63:3154.
31. Stock HT, Turner NJ. Tetrahedron Lett. 1996;37:6575.
32. Slebioda M, St-Amand MA, Chen FMF, Benoiton NL. Can. J. Chem. 1988;66:2540.
33. Seebach D, Jaeschke G, Wang YM. Angew. Chem. 1995; 107:2605; Angew. Chem. Int. Ed. Engl.1995;34:2395.
34. Seebach D, Jaeschke G, Wang YM. Angew. Chem. 1995; 107:2605; Angew. Chem. Int. Ed. Engl.1995;34:2395.
35. Jaeschke G, Seebach D, J. Org. Chem. 1998;63:1190.
36. Ramon DJ, Guillena G, Seebach D. Helv. Chim. Acta 1996;79:875.
37. Narasaka K, Kanai F, Okudo M, Miyoshi N. Chem. Lett. 1989:1187.
38. Seebach D, Jaeschke G, Gottwald K, Matsuda K, Formisano R, Chaplin DA, Breuning M, Bringmann G. Tetrahedron 1997;53:7539.
39. Goodman M, Glaser CB. J. Org. Chem. 1970;35:1954.
40. Cornforth JW. In: Clarke HT, Johnson JR, Robinson R, editors. The Chemistry of Penicillin. Princeton, New Jersey: Princeton University Press, 1949:688.
41. Meyer RF, Nicolaides ED, Tinney FJ, Lunney EA, Holmes A, Hoefle ML. J. Med. Chem. 1981;24:964.
42. Godunova LF, Levitina ES, Karpeiskaya EI, Klabunovskii EI, Yagupol'skii YL, Kolycheva MT. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1989;38:351.
43. Carter HE, Handler P, Melville DE. J. Biol. Chem. 1939;129:359.
44. Lamb J, Robson W. Biochem. J. 1931;25:1231.
45. Similar problems have been discussed in the literature: Ali M, Khan NH, Siddiqui AA. Synth. Commun. 1976;6:227.
46. Wong HNC, Xu ZL, Chang HM, Lee CM. Synthesis 1992:793.
47. Siemion IZ, Baran G. Bull. Acad. Pol. Sci. 1975;23:317.
48. Chen FMF, Benoiton NL. Int. J. Peptide Protein Res. 1987;30:683.
49. Toniolo C, Valle G, Formaggio F, Crisma M, Boesten WHJ, Polinelli S, Schoemaker HE, Kamphuis J. J. Chem. Soc. Perkin Trans. 1 1991:3386.
50. Valle G, Crisma M, Pantano M, Formaggio F, Toniolo C, Kamphuis J. Zeit. Kristallogr. 1993,208:259.
51. Crisma M, Valle G, Moretto V, Formaggio F, Toniolo C. Peptide Research 1995;8:187.
52. Fujiwara H, Van der Veen JM. J. Chem. Soc. Perkin 2 1979:659.
53. Madison V, Young PE, Blout ER. J. Am. Chem. Soc. 1976;98:5358.
54. Gotthardt H, Huisgen R, Bayer HO. J. Am. Chem. Soc. 1970;92:4340.
55. Hoefle G, Steglich W, Daniel H. Chem. Ber. 1976;109:2648.
56. Schmidt B, Seebach D. Angew. Chem. 1991;103:100; Angew. Chem. Int. Ed. Engl. 1991;30:99.
57. Schmidt B, Seebach D. Angew. Chem. 1991;103:100; Angew. Chem. Int. Ed. Engl. 1991;30:99.
58. Schmidt B, Seebach D. Angew. Chem. 1991;103:1383; Angew. Chem. Int. Ed. Engl. 1991:30:1321.
59. Schmidt B, Seebach D. Angew. Chem. 1991;103:1383; Angew. Chem. Int. Ed. Engl. 1991:30:1321.
60. Seebach D, Beck AK, Schmidt B, Wang YM. Tetrahedron 1994;50:4363.
61. Seebach D, Plattner DA, Beck AK, Wang YM, Hunziker D, Petter W. Helv. Chim. Acta 1992;75:2171.
62. Carter HE. Org. React. 1946;3:198.
63. Griffith RK, Harwood HJ. J. Org. Chem. 1964;29:2658.
64. Tripathy PK, Mukerjee AK. Synthesis 1984:418.
65. Greenstein JB, Winitz MW. Chemistry of the Amino Acids. New York: Wiley, 1961;1267.
66. Rao YS. J. Org. Chem. 1976;41:722.
67. Taudien S, SchinkowsKi K, Krause H-W. Tetrahedron: Asymmetry 1993;4:73.
68. Thondorf I, Strube M. Z. Chem. 1988;28:330.
69. Mustafa A, Sallam MMM. J. Org. Chem. 1962;27:2406.
70. Devasia GM, Pillai CR. Tetrahedron Lett. 1975; 16:4051.
71. Badshah A, Khan NH, Kidwai AR. J. Org. Chem. 1972;37:2916.
72. Kikkoji T. Biochem. Z. 1911;35:57.
73. Ali M, Khan NH, Siddiqui AA. Synth. Commun. 1976;6:227.
74. Kolb M, Barth J, Neises B. Tetrahedron Lett. 1986;27:1579.